No need to plan your next long weekend. We have curated the perfect itinerary for a stay at the Islands of Islamorada. Just pack your bags and let our team handle the rest.
Thursday: Settle In & Soak it Up
Check-In:
Arrive at 4 PM and let the vacation begin. As you step into The Islands of Islamorada, we’ll welcome you with a refreshing tropical drink—our way of easing you into Island Time from the very first moment. After a quick property overview, a dedicated team member will personally escort you to your suite or villa, ensuring a seamless and relaxed start to your stay.
Morada Art Walk:
In the evening, explore the local culture by visiting the Morada Art Walk, a vibrant showcase of local art, live music, and crafts. It’s a wonderful way to immerse yourself in the laid-back island atmosphere and connect with Islamorada’s artistic community. (Every third Thursday of the month from 6-9p)
Sunset Swim:
Once back on the property, head to the poolside tiki bar. Sip on a refreshing cocktail as you take a dip, enjoying the setting sun and beautiful ocean views. It’s the perfect way to unwind after travel.
Friday: A Full Islands Experience
Morning Yoga:
Start your day with a yoga class on the Ocean House Lawn. The serene setting, with the sound of waves gently lapping in the background, will leave you feeling grounded and rejuvenated as a local yogi guides you through a flow.
Biking to Breakfast at Bitton Bistro Café:
After yoga, take a leisurely bike ride to Bitton Bistro Café, a charming, locally owned spot offering handmade French cuisine. This hidden gem is known for its warm atmosphere and delicious, authentic dishes crafted from fresh ingredients. Whether you’re in the mood for a croissant sandwich, a savory quiche, or a perfectly brewed espresso, this café is a great way to experience a taste of France right in Islamorada.
Enjoying the Water Sports:
Once back on the property, it's time to hit the water! Paddleboarding in the ocean is a great way to explore the marine life and take in the stunning views. For more adventure, hop on a Hobie Cat and sail along the coast. The feeling of the wind in your hair and the sun on your skin will make for an exhilarating experience.
Order Fresh Seasonal Fare for Dinner:
For dinner, indulge in the fresh flavors of the Florida Keys. Our team can help arrange for locally sourced seafood and island-inspired dishes to be prepared and served right in the comfort of your villa. It’s a deliciously effortless way to end the day—with a taste of the tropics, no reservations required.
Sunset Cruise:
After dinner, embark on a sunset cruise with Captain Rob to fully embrace the magic of Islamorada. Watching the sky turn vivid shades of orange, pink, and purple as you sail the crystal-clear waters will be a highlight of your trip. Toast with a glass of champagne and savor the moment. All arranged by the concierge.
Sweet Treat:
After dinner, gather around one of the resort’s fire pits for some fun with the family. Roast s’mores under the stars, the perfect end to your first full day at the Islands of Islamorada.
Saturday: Adventure & Sunset Views
Enjoy the Water:
Islamorada is known as the “Sportfishing Capital of the World,” offering a wide variety of boat excursions to suit every kind of adventurer. You can choose to spend the morning fishing for dinner or diving for lobsters. If you’d rather opt for a more laid-back experience like snorkeling the stunning coral reefs, this is the place to do it. If you're in the mood for a truly local experience, consider heading out to the sandbar—a weekend hotspot where hundreds of locals raft their boats together, creating a fun, festive atmosphere. Food truck boats serving fresh ceviche and crispy tostones will make your sandbar visit all the more delicious.
Key Lime Trail:
The Florida Keys’ signature citrus flavor isn’t just for pie—it’s infused into ice cream, cocktails, seafood, and even beer. We invite you to explore it all on The Islands of Islamorada's new Key Lime Culinary Trail, our resort curated self-guided tasting tour featuring some of our concierge team's favorites from the island’s most beloved Key lime-infused treats.
With complimentary bike rentals available for guests, you can cruise along the coast and stop at iconic cafés, seafood hotspots, breweries, and sweet shops, all within a three-mile radius of the resort.
Divine Local Dining:
For dinner, head over to Chef Michael’s, a quick drive from the resort, where you’ll be treated to a world-class culinary experience. With expertise honed in from top the restaurants of Manhattan to Martinique, the chefs at Chef Michael’s take pride in presenting an exquisite menu of fresh seafood and local ingredients. If you were lucky on the water, you can bring your fresh catch to be prepared in a variety of ways. The attentive staff will make sure your evening is as enjoyable as the food itself, offering a perfect close to your day.
Sunday: A Relaxing Send-Off
Morning Swim:
Before packing up, take a refreshing morning swim in one of the pools. The tranquil waters will leave you feeling relaxed and ready to ease back into reality.
Pack Up and Head Home:
After breakfast, it’s time to pack up and check out. Our concierge will handle the coordination of your transportation, making your transition home as easy as your arrival. Take in the final views as you head out—already dreaming of your next island escape.
One Last Local Adventure:
If your travel plans allow, head to 81001 Overseas Highway for the Florida Keys Farmers Market every Sunday from 10a-3p. You’ll find fresh local produce, handmade goods, food trucks, and live music — making it a great way to spend a laid-back weekend morning in the Keys.